IMPPAT Phytochemical information: 
Smilageninoside
Smilageninoside
Summary

SMILES: OC[C@H]1O[C@@H](OC2CC[C@]3(C(C2)CCC2C3CC[C@]3(C2C[C@H]2[C@@H]3[C@H](C)C3(O2)CC[C@H](CO3)C)C)C)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C39H64O13/c1-18-7-12-39(47-17-18)19(2)28-25(52-39)14-24-22-6-5-20-13-21(8-10-37(20,3)23(22)9-11-38(24,28)4)48-36-34(32(45)30(43)27(16-41)50-36)51-35-33(46)31(44)29(42)26(15-40)49-35/h18-36,40-46H,5-17H2,1-4H3/t18-,19+,20?,21?,22?,23?,24?,25+,26-,27-,28+,29-,30-,31+,32+,33-,34+,35+,36-,37+,38+,39?/m1/s1
InChIKey: MMTWXUQMLQGAPC-ZKXXMABPSA-N
DeepSMILES: OC[C@H]O[C@@H]OCCC[C@]CC6)CCCC6CC[C@]C6C[C@H][C@@H]5[C@H]C)CO5)CC[C@H]CO6))C))))))))))C)))))))))C))))))[C@H][C@H][C@@H]6O))O))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCC(OC2CCCOC2OC2CCC3C(CCC4C3CCC3C5CC6(CCCCO6)OC5CC34)C2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCCOC2OC2CCC3C(CCC4C3CCC3C5CC6(CCCCO6)OC5CC34)C2)OC1
Scaffold Graph level: C1CCC(CC2CCCCC2CC2CCC3C(CCC4C3CCC3C5CC6(CCCCC6)CC5CC34)C2)CC1
Functional groups: CO; CO[C@@H](C)OC; COC(C)(C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Spirostane steroids
Synonymous chemical names:
smilageninoside, Smilageninoside
External chemical identifiers:
CID:CID_197391
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Smilageninoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 740.93
Log P RDKit 1.44
Topological polar surface area (Å2) RDKit 196.99
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 22
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 39
Shape complexity RDKit 1
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Smilageninoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.19
Smilageninoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.48
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes